Patent GB-2380192-A (GB)
Title: Liquid crystalline phenylacetylenes with highest occupied molecular orbital (HOMO) energy relationship or based on dibenzothiophene, and precursors therefor
Inventor: SEKINE CHIZU
IPC: C09K19/18
Filed: 2002-02-07
Abstract: There are disclosed novel compounds of formulae (1), (2), (A-1), (A-2), (A-3) and (A-4); polymers obtained by polymerisation of such compounds; and liquid crystal compositions, optically anisotropic products, and optical or liquid crystal elements that comprise such compounds and polymers. These compounds have large refractive index anisotropy, mix easily with other liquid crystals, have advantageous stability against light, and exhibit absorption at practically short wavelength in the ultraviolet region.<BR> ```wherein A<SP>1</SP> to A<SP>4</SP> each independently stands for a hydrogen atom, a fluorine atom, or an alkyl or alkoxy group having 1 to 10 carbon atoms optionally substituted with at least one fluorine atom; and P<SP>1</SP> and P<SP>2</SP> have any chemical structures as long as P<SP>1</SP> and P<SP>2</SP> satisfy the conditions <SL> <LI>(i) the difference   W  E in energy of the highest occupied molecular orbital (HOMO) of parts of the formula (1) each represented by the formula (1-1), (1-2) or (1-3) satisfies the formula:<BR> <BR>   W  E = E 1-1 -(E 1-2 +E 1-3 )/2   /   0 .3 electronvolt<BR> <BR> ```wherein E 1-1 , E 1-2 , and E 1-3  denote the HOMO energy of corresponding parts represented by the formulae (1-1), (1-2), and (1-3), respectively, of the formula (1) calculated by the method of molecular orbitals, and <LI>(ii) the polarizability anisotropy   Wa   of a molecule represented by the formula (1) calculated by the method is not lower than 500 atomic units. </SL> <BR> ```wherein A<SP>9</SP> to A<SP>12</SP> are independently as defined for A<SP>1</SP> to A<SP>4</SP>; P<SP>3</SP> and P<SP>4</SP> each stands for the formula (2-1) or (2-2), with at least one of P<SP>3</SP> and P<SP>4</SP> standing for the formula (2-1)<BR> ```wherein A<SP>37</SP> to A<SP>42</SP> in the formula (2-1) and A<SP>5</SP> to A<SP>8</SP> in the formula (2-2) are independently as defined for A<SP>1</SP> to A<SP>4</SP>,<BR> R<SP>11</SP> and R<SP>12</SP> each independently stands for a hydrogen atom, a fluorine atom, a cyano group, -SF 5 , -NCS, a 4-R<SP>23</SP>-(cycloalkyl) group, a 4-R<SP>23</SP>-(cycloalkenyl) group, and R<SP>24</SP>-(O)q group, or a group represented by the formula (3), wherein R<SP>23</SP> stands for a hydrogen atom, or a straight or branched alkyl group having 1 to 12 carbon atoms optionally substituted with at least one fluorine atom, R<SP>24</SP> stands for a straight or branched alkyl group having 1 to 12 carbon atoms optionally substituted with at least one fluorine atom, or a straight or branched alkenyl or alknyl group having 3 to 12 carbon atom optionally substituted with at least one fluorine atom, q denotes 0 or 1,<BR> ```wherein n denotes 0 or 1, and m denotes and integer of 1 to 20, B<SP>1</SP> stands for a hydrogen atom or a methyl group, when both R<SP>11</SP> and R<SP>12</SP> stand for a group represented by the formula (3), n, m, and B<SP>1</SP> in one group of the formula (3) may be the same as or different from those of the other.<BR> ```wherein A<SP>1</SP> to A<SP>6</SP> are independently as defined for A<SP>1</SP> to A<SP>4</SP>, X stands for a halogen atom, and Y stands for a halogen atom or a hydroxyl group.